diff --git a/backend/open_webui/utils/context_compaction.py b/backend/open_webui/utils/context_compaction.py
index 1c09b8155f..87aa9335ca 100644
--- a/backend/open_webui/utils/context_compaction.py
+++ b/backend/open_webui/utils/context_compaction.py
@@ -145,6 +145,10 @@ async def compact_messages_for_request(
                     'action': 'context_compaction',
                     'description': 'Context compacted',
                     'done': True,
+                    'checkpoint_message_id': (
+                        recent_messages[0].get('id') if recent_messages[0].get('role') == 'user' else None
+                    ),
+                    'context_summary': summary,
                 },
             }
         )
diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index 7f8436e1cf..e148b5a989 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -87,7 +87,7 @@ from open_webui.utils.access_control.files import get_owner_accessible_folder_fi
 from open_webui.utils.access_control.folders import has_folder_access
 from open_webui.utils.ask_user import stage_ask_user_tool_calls
 from open_webui.utils.chat import generate_chat_completion
-from open_webui.utils.chat_id import is_saved_chat_id
+from open_webui.utils.chat_id import is_saved_chat_id, is_temporary_chat_id
 from open_webui.utils.code_interpreter import execute_code_jupyter
 from open_webui.utils.context_compaction import compact_messages_for_request
 from open_webui.utils.files import (
@@ -2137,7 +2137,7 @@ async def process_chat_payload(request, form_data, user, metadata, model):
     if regeneration_prompt:
         form_data['messages'].append({'role': 'user', 'content': regeneration_prompt})
 
-    if is_saved_chat_id(chat_id) and user_message_id:
+    if (is_saved_chat_id(chat_id) or is_temporary_chat_id(chat_id)) and user_message_id:
         system_message = get_system_message(form_data.get('messages', []))
         chat_system_prompt = get_content_from_message(system_message) if system_message else ''
 
diff --git a/src/lib/components/chat/Chat.svelte b/src/lib/components/chat/Chat.svelte
index 366c0770f9..754dbf3061 100644
--- a/src/lib/components/chat/Chat.svelte
+++ b/src/lib/components/chat/Chat.svelte
@@ -1588,6 +1588,9 @@
 						message.statusHistory = [data];
 					}
 				} else if (type === 'context_compaction') {
+					if (data?.checkpoint_message_id && history.messages[data.checkpoint_message_id]) {
+						history.messages[data.checkpoint_message_id].contextSummary = data.context_summary;
+					}
 					handleContextCompactionStatus(data);
 				} else if (type === 'chat:active') {
 					if (!data?.active) {
@@ -4254,7 +4257,9 @@
 
 					if (message.role === 'user' && imageFiles.length > 0) {
 						return {
+							id: message.id,
 							role: message.role,
+							contextSummary: message?.contextSummary,
 							content: [
 								{
 									type: 'text',
@@ -4271,7 +4276,9 @@
 					}
 
 					return {
+						id: message.id,
 						role: message.role,
+						contextSummary: message?.contextSummary,
 						content: message?.merged?.content ?? message.content,
 						model: message.model,
 						meta: message.meta